The article examines the second career teachers (SCTs) socialisation into school culture through three theoretical lenses: Bronfenbrenner's ecological framework of human development, to identify the different environments within school culture that play a role in SCTs perceptions of their socialisation, Lave and Wenger's theory of Legitimate Peripheral Participation and Bridge's Transition Model (Bridges, 1991; Bridges & Mitchell, 2000) to characterize the modes of transition teachers face. This is likely to guide school administrators to view SCTs as a unique group of teachers whose starting point is different from the other novice teachers, due to the knowledge capital they bring with them to the socialisation process. It is argued that school management need to be aware of the fragile 'transition' phase of the novice SCTs. For some teachers who lack the agency to take initiatives and act proactively, this might be a trying phase of sink or swim. In schools where the interpersonal relationships within the ecological culture of the school were supportive, teachers felt more confident to socialise, while in schools where teachers felt lonely and 'forsaken to manage on their own', their self-image was vulnerable. Schools should provide opportunities for the teachers to manage the transition effectively by creating a cooperative environment within the school and establishing organisational practices.